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822-06-0
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Identification
Name
1,6-Diisocyanatohexane
CAS
822-06-0
Synonyms
1,6-Diisocyantohexane
1,6-HEXAMETHYLENE DIISOCYANATE
Hexamethylene-1,6-diisocyanate
HEXAMETHYLENE DIISOCYANATE
1,6-diisocyanated’hexamethylene
1,6-diisocyanato-hexan
1,6-hexanedioldiisocyanate
1,6-Hexylene diisocyanate
1,6-hexylenediisocyanate
desmodurh
desmodurn
hexamethylendiisokyanat
Hexane 1,6-diisocyanate
Hexane, 1,6-diisocyanato-
hexane,1,6-diisocyanato-
hexane-1,6-diisocyanate
hexane1,6-diisocyanate
Isocyanic acid, diester with 1,6-hexanediol
Isocyanic acid, hexamethylene ester
isocyanicacid,diesterwith1,6-hexanediol
EINECS(EC#)
212-485-8
Molecular Formula
C8H12N2O2
MDL Number
MFCD00002047
Molecular Weight
168.19
MOL File
822-06-0.mol
1,6-Diisocyanatohexane
CAS
822-06-0
Synonyms
1,6-Diisocyantohexane
1,6-HEXAMETHYLENE DIISOCYANATE
Hexamethylene-1,6-diisocyanate
HEXAMETHYLENE DIISOCYANATE
1,6-diisocyanated’hexamethylene
1,6-diisocyanato-hexan
1,6-hexanedioldiisocyanate
1,6-Hexylene diisocyanate
1,6-hexylenediisocyanate
desmodurh
desmodurn
hexamethylendiisokyanat
Hexane 1,6-diisocyanate
Hexane, 1,6-diisocyanato-
hexane,1,6-diisocyanato-
hexane-1,6-diisocyanate
hexane1,6-diisocyanate
Isocyanic acid, diester with 1,6-hexanediol
Isocyanic acid, hexamethylene ester
isocyanicacid,diesterwith1,6-hexanediol
EINECS(EC#)
212-485-8
Molecular Formula
C8H12N2O2
MDL Number
MFCD00002047
Molecular Weight
168.19
MOL File
822-06-0.mol
Chemical Properties
Appearance
colourless liquid
Appearance
Hexamethylene diisocyanate is a colorless liquid. Sharp, irritating odor.
Melting point
-55°C
mp
-55°C
Boiling point
82-85 °C0.1 mm Hg
bp
82-85 °C0.1 mm Hg
density
1.047 g/mL at 20 °C(lit.)
vapor pressure
0.05 mm Hg ( 25 °C)
refractive index
n20/D 1.453
Fp
248 °F
storage temp.
2-8°C
form
Liquid
Specific Gravity
1.05
color
Clear colorless to slightly yellow
Stability:
Stable. Moisture sensitive. Combustible. Incompatible with strong oxidizing agents, strong bases, amines, acids. May react explosively with alcohols in the presence of base without a diluting solvent. Heating above 200 C may cause polymerization.
explosive limit
0.9-9.5%(V)
Water Solubility
Reacts
Sensitive
Moisture Sensitive
BRN
956709
Exposure limits
TLV-TWA 0.0343 mg/m3 (0.005 ppm) (ACGIH).
Contact allergens
This diisocyanate compound is used in the manufac ture of various polyurethane products: elastic and rigid foams, paints, lacquers, adhesives, binding agents, synthetics rubbers, and elastomer fibers.
InChIKey
RRAMGCGOFNQTLD-UHFFFAOYSA-N
Uses
Chemical intermediate.
CAS DataBase Reference
822-06-0(CAS DataBase Reference)
NIST Chemistry Reference
1,6-Hexamethylene diisocyanate(822-06-0)
EPA Substance Registry System
822-06-0(EPA Substance)
colourless liquid
Appearance
Hexamethylene diisocyanate is a colorless liquid. Sharp, irritating odor.
Melting point
-55°C
mp
-55°C
Boiling point
82-85 °C0.1 mm Hg
bp
82-85 °C0.1 mm Hg
density
1.047 g/mL at 20 °C(lit.)
vapor pressure
0.05 mm Hg ( 25 °C)
refractive index
n
Fp
248 °F
storage temp.
2-8°C
form
Liquid
Specific Gravity
1.05
color
Clear colorless to slightly yellow
Stability:
Stable. Moisture sensitive. Combustible. Incompatible with strong oxidizing agents, strong bases, amines, acids. May react explosively with alcohols in the presence of base without a diluting solvent. Heating above 200 C may cause polymerization.
explosive limit
0.9-9.5%(V)
Water Solubility
Reacts
Sensitive
Moisture Sensitive
BRN
956709
Exposure limits
TLV-TWA 0.0343 mg/m3 (0.005 ppm) (ACGIH).
Contact allergens
This diisocyanate compound is used in the manufac ture of various polyurethane products: elastic and rigid foams, paints, lacquers, adhesives, binding agents, synthetics rubbers, and elastomer fibers.
InChIKey
RRAMGCGOFNQTLD-UHFFFAOYSA-N
Uses
Chemical intermediate.
CAS DataBase Reference
822-06-0(CAS DataBase Reference)
NIST Chemistry Reference
1,6-Hexamethylene diisocyanate(822-06-0)
EPA Substance Registry System
822-06-0(EPA Substance)
Hazard Information
Chemical Properties
colourless liquid
Definition
ChEBI: A diisocyanate compound with the two isocyanates linked by a hexane-1,6-diyl group.
General Description
A colorless crystalline solid. Toxic by ingestion and is strongly irritating to skin and eyes. HEXAMETHYLENE DIISOCYANATE(822-06-0) is used to make nylon.
Reactivity Profile
HEXAMETHYLENE DIISOCYANATE reacts with water. Base-catalyzed reactions of this compound with alcohols may be explosively violent in the absence of diluting solvents. This chemical is incompatible with strong bases, amines, acids and strong oxidizers. HEXAMETHYLENE DIISOCYANATE is also incompatible with metal compounds and surface active materials. .
Air & Water Reactions
Contact with moisture or temperatures over 399°F may cause polymerization. Soluble in water.
Hazard
Combustible.
Health Hazard
TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Potential Exposure
Used to make other chemicals, coat ings, and polyurethane. It is also used as a hardener in automobile and airplane paints.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, includ ing resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medi cal attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
Fire Hazard
Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Shipping
UN2281 Hexamethylene diisocyanate, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
May form explosive mixture with air. Isocyanates are highly flammable and reactive with many compounds, even with themselves. Incompatible with oxi dizers (chlorates, nitrates, peroxides, permanganates, per chlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Reaction with moist air, water or alcohols may form amines and insoluble polyureas and react exothermically, releasing toxic, corrosive or flamma ble gases, including carbon dioxide; and, at the same time, may generate a violent release of heat increasing the con centration of fumes in the air. Incompatible with amines, aldehydes, alkali metals, ammonia, carboxylic acids, capro lactum, alkaline materials, glycols, ketones, mercaptans, hydrides, organotin catalysts, phenols, strong acids, strong bases, strong reducing agents such as hydrides, urethanes, ureas. Elevated temperatures or contact with acids, bases, tertiary amines, and acyl-chlorides may cause explosive polymerization. Attacks some plastics, rubber and coatings. Contact with metals may evolve flammable hydrogen gas. May accumulate static electrical charges, and may cause ignition of its vapors. Temperatures above 200℃ can cause polymerization. Attacks copper.
Description
This diisocyanate compound is used in the manufacture of various polyurethane products: elastic and rigid foams, paints, lacquers, adhesives, bin ding agents, synthetic rubbers, and elastomeric fibers.
Preparation
Hexamethylene diisocyanate (HDI) is prepared by the phosgenation of hexamethylenediamine (section lO.2.2(b)):
H2N-(CH2)6-NH2--COCl2-->OCN-(CH2)6-NCO
Hexamethylene diisocyanate is a liquid with a volatility of the same order as that of tolylene diisocyanate. It is respiratory irritant and also has powerful effects on the skin and eyes. Hexamethylene diisocyanate was one of the first diisocyanates utilized for making polyurethanes, being used to prepare fibres and moulding compounds. These applications are no longer of importance but hexamethylene diisocyanate now finds use mainly in coatings which are more light stable than those based on aromatic isocyanates.
Application
Hexamethylene diisocyanate is an aliphatic diisocyanate monomer typically used to produce oligomers and prepolymers that when combined with a polyol produce light-stable polyurethane.
Highly reactive 1,6-hexamethylene diisocyanate (HMDI) was used to synthesize lactic acid polymers from oligomers by the addition of 2,2′-bis(2-oxazoline) (BOX) as chain extenders. Self-healing ability was rendered to polyurethane elastomer by synthesizing alkoxyamine-based diol and reacting it with tri-functional homopolymer of HMDI and polyethylene glycol (PEG). Plastic optical fiber (POF) was prepared by the bulk homopolymerization of HMDI catalyzed by Tin(II)-2 ethylhexanoate (SnOct).
Environmental Fate
HDI is not readily soluble (low mg l-1 range) in water. However, upon contact with water, reactivity is rapid with a half-life of 0.23 h at 23 ℃. This nonhomogeneous reaction is expected to produce principally polyureas. In the occupational environment, an aerosol can be formed by nebulization; however, with a vapor pressure of 0.007 hPa, HDI is expected to exist in the ambient atmosphere in its vapor state. As a vapor, HDI is expected to degrade in the atmosphere by reaction with hydroxyl radicals (half-life approximately 2 days). In direct contact with water, its rapid hydrolysis reduces the likelihood for HDI to bioaccumulate in the aquatic compartment or transfer to groundwater. Therefore, the rapid hydrolysis in an aquatic environment and relatively rapid degradation in atmosphere limits the ability of this substance to be bioaccumulative or persistent.
Toxicity evaluation
Toxicity predominantly results from direct interaction of HDI with tissues or macromolecules at the portal of entry. HDI reacts with biologic macromolecules containing nucleophilic –NH, –SH, –OH, or –COOH groups, and these interactions are thought to account for acute irritation to skin and mucus membranes, sensory irritation, and dermal sensitization. Less clear is the etiology of HDI-induced occupational asthma. A number of mechanisms, including immunologic, neurologic, and pharmacologic, have been postulated without a clear resolution. Overall, these mechanisms account for the principal effects associated with HDI that lead to toxicity at the portal of entry with no evidence of primary systemic organ toxicity.
Waste Disposal
Disposal is by chemical incineration of HDIsolution in a combustible solvent.
colourless liquid
Definition
ChEBI: A diisocyanate compound with the two isocyanates linked by a hexane-1,6-diyl group.
General Description
A colorless crystalline solid. Toxic by ingestion and is strongly irritating to skin and eyes. HEXAMETHYLENE DIISOCYANATE(822-06-0) is used to make nylon.
Reactivity Profile
HEXAMETHYLENE DIISOCYANATE reacts with water. Base-catalyzed reactions of this compound with alcohols may be explosively violent in the absence of diluting solvents. This chemical is incompatible with strong bases, amines, acids and strong oxidizers. HEXAMETHYLENE DIISOCYANATE is also incompatible with metal compounds and surface active materials. .
Air & Water Reactions
Contact with moisture or temperatures over 399°F may cause polymerization. Soluble in water.
Hazard
Combustible.
Health Hazard
TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Potential Exposure
Used to make other chemicals, coat ings, and polyurethane. It is also used as a hardener in automobile and airplane paints.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, includ ing resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medi cal attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
Fire Hazard
Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Shipping
UN2281 Hexamethylene diisocyanate, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
May form explosive mixture with air. Isocyanates are highly flammable and reactive with many compounds, even with themselves. Incompatible with oxi dizers (chlorates, nitrates, peroxides, permanganates, per chlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Reaction with moist air, water or alcohols may form amines and insoluble polyureas and react exothermically, releasing toxic, corrosive or flamma ble gases, including carbon dioxide; and, at the same time, may generate a violent release of heat increasing the con centration of fumes in the air. Incompatible with amines, aldehydes, alkali metals, ammonia, carboxylic acids, capro lactum, alkaline materials, glycols, ketones, mercaptans, hydrides, organotin catalysts, phenols, strong acids, strong bases, strong reducing agents such as hydrides, urethanes, ureas. Elevated temperatures or contact with acids, bases, tertiary amines, and acyl-chlorides may cause explosive polymerization. Attacks some plastics, rubber and coatings. Contact with metals may evolve flammable hydrogen gas. May accumulate static electrical charges, and may cause ignition of its vapors. Temperatures above 200℃ can cause polymerization. Attacks copper.
Description
This diisocyanate compound is used in the manufacture of various polyurethane products: elastic and rigid foams, paints, lacquers, adhesives, bin ding agents, synthetic rubbers, and elastomeric fibers.
Preparation
Hexamethylene diisocyanate (HDI) is prepared by the phosgenation of hexamethylenediamine (section lO.2.2(b)):
H2N-(CH2)6-NH2--COCl2-->OCN-(CH2)6-NCO
Hexamethylene diisocyanate is a liquid with a volatility of the same order as that of tolylene diisocyanate. It is respiratory irritant and also has powerful effects on the skin and eyes. Hexamethylene diisocyanate was one of the first diisocyanates utilized for making polyurethanes, being used to prepare fibres and moulding compounds. These applications are no longer of importance but hexamethylene diisocyanate now finds use mainly in coatings which are more light stable than those based on aromatic isocyanates.
Application
Hexamethylene diisocyanate is an aliphatic diisocyanate monomer typically used to produce oligomers and prepolymers that when combined with a polyol produce light-stable polyurethane.
Highly reactive 1,6-hexamethylene diisocyanate (HMDI) was used to synthesize lactic acid polymers from oligomers by the addition of 2,2′-bis(2-oxazoline) (BOX) as chain extenders. Self-healing ability was rendered to polyurethane elastomer by synthesizing alkoxyamine-based diol and reacting it with tri-functional homopolymer of HMDI and polyethylene glycol (PEG). Plastic optical fiber (POF) was prepared by the bulk homopolymerization of HMDI catalyzed by Tin(II)-2 ethylhexanoate (SnOct).
Environmental Fate
HDI is not readily soluble (low mg l-1 range) in water. However, upon contact with water, reactivity is rapid with a half-life of 0.23 h at 23 ℃. This nonhomogeneous reaction is expected to produce principally polyureas. In the occupational environment, an aerosol can be formed by nebulization; however, with a vapor pressure of 0.007 hPa, HDI is expected to exist in the ambient atmosphere in its vapor state. As a vapor, HDI is expected to degrade in the atmosphere by reaction with hydroxyl radicals (half-life approximately 2 days). In direct contact with water, its rapid hydrolysis reduces the likelihood for HDI to bioaccumulate in the aquatic compartment or transfer to groundwater. Therefore, the rapid hydrolysis in an aquatic environment and relatively rapid degradation in atmosphere limits the ability of this substance to be bioaccumulative or persistent.
Toxicity evaluation
Toxicity predominantly results from direct interaction of HDI with tissues or macromolecules at the portal of entry. HDI reacts with biologic macromolecules containing nucleophilic –NH, –SH, –OH, or –COOH groups, and these interactions are thought to account for acute irritation to skin and mucus membranes, sensory irritation, and dermal sensitization. Less clear is the etiology of HDI-induced occupational asthma. A number of mechanisms, including immunologic, neurologic, and pharmacologic, have been postulated without a clear resolution. Overall, these mechanisms account for the principal effects associated with HDI that lead to toxicity at the portal of entry with no evidence of primary systemic organ toxicity.
Waste Disposal
Disposal is by chemical incineration of HDIsolution in a combustible solvent.
Safety Data
Hazard Codes
T
Risk Statements
R23:Toxic by inhalation.
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact .
Safety Statements
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
RIDADR
UN 2281 6.1/PG 2
WGK Germany
1
RTECS
MO1740000
F
10-19-21
Autoignition Temperature
454 °C
TSCA
Yes
HazardClass
6.1
PackingGroup
II
HS Code
29291090
Safety Profile
Poison by inhalation and intravenous routes. Moderately toxic by ingestion and skin contact. Potentially explosive reaction with alcohols + base. When heated to decomposition it emits toxic fumes of NOx. See also CYANATES.
Hazardous Substances Data
822-06-0(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 746 mg/kg LD50 dermal Rabbit 570 mg/kg
T
Risk Statements
R23:Toxic by inhalation.
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact .
Safety Statements
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
RIDADR
UN 2281 6.1/PG 2
WGK Germany
1
RTECS
MO1740000
F
10-19-21
Autoignition Temperature
454 °C
TSCA
Yes
HazardClass
6.1
PackingGroup
II
HS Code
29291090
Safety Profile
Poison by inhalation and intravenous routes. Moderately toxic by ingestion and skin contact. Potentially explosive reaction with alcohols + base. When heated to decomposition it emits toxic fumes of NOx. See also CYANATES.
Hazardous Substances Data
822-06-0(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 746 mg/kg LD50 dermal Rabbit 570 mg/kg
Raw materials And Preparation Products
Raw materials
Diethyl ether-->Tetrahydrofuran-->Ammonia-->Adipic acid-->Diphenylphosphoryl azide-->1,6-HEXANEDIAMINE-->Film evaporator-->Biuret-->Suberic acid-->1,8-Bis(dimethylamino)naphtalene
Preparation Products
EAM resin adhesive modified with diisocyanate for orthodontias-->CC-2SH adhesive composite used in anterior teeth
Diethyl ether-->Tetrahydrofuran-->Ammonia-->Adipic acid-->Diphenylphosphoryl azide-->1,6-HEXANEDIAMINE-->Film evaporator-->Biuret-->Suberic acid-->1,8-Bis(dimethylamino)naphtalene
Preparation Products
EAM resin adhesive modified with diisocyanate for orthodontias-->CC-2SH adhesive composite used in anterior teeth
Material Safety Data Sheet(MSDS)
Spectrum Detail
Spectrum Detail
Hexamethylene Diisocyanate(822-06-0)MS
Hexamethylene Diisocyanate(822-06-0)1HNMR
Hexamethylene Diisocyanate(822-06-0)13CNMR
Hexamethylene Diisocyanate(822-06-0)IR1
Hexamethylene Diisocyanate(822-06-0)IR2
Hexamethylene Diisocyanate(822-06-0)Raman
Hexamethylene Diisocyanate(822-06-0)MS
Hexamethylene Diisocyanate(822-06-0)1HNMR
Hexamethylene Diisocyanate(822-06-0)13CNMR
Hexamethylene Diisocyanate(822-06-0)IR1
Hexamethylene Diisocyanate(822-06-0)IR2
Hexamethylene Diisocyanate(822-06-0)Raman
Well-known Reagent Company Product Information
Acros Organics
1,6-Diisocyanatohexane, 99+%(822-06-0)
Alfa Aesar
1,6-Diisocyanatohexane, 98+%(822-06-0)
Sigma Aldrich
822-06-0(sigmaaldrich)
TCI AMERICA
Hexamethylene Diisocyanate,>98.0%(GC)(822-06-0)
1,6-Diisocyanatohexane, 99+%(822-06-0)
Alfa Aesar
1,6-Diisocyanatohexane, 98+%(822-06-0)
Sigma Aldrich
822-06-0(sigmaaldrich)
TCI AMERICA
Hexamethylene Diisocyanate,>98.0%(GC)(822-06-0)
SupplierMore
- Shanghai Aladdin Bio-Chem Technology Co.,LTD
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