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123-30-8

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Identification

Name
4-Aminophenol
CAS
123-30-8
Synonyms
4-AMINO-1-HYDROXYBENZENE
4-AMINOPHENOL
4-HYDROXYANILINE
4-HYROXYANILINE
ACETAMINOPHEN IMPURITY K
AMINOPHENOL-4
AZOL
CERTINAL
CITOL
HYDROCODONE/APAP BITARTRATE IMP K
JAROCOL PAP
LABOTEST-BB LTBB000486
p-Aminophenc
P-AMINOPHENOL
PARA AMINO PHENOL
PARANOL
P-HYDROXYANILINE
1-Amino-4-hydroxybenzene
4-Amino-1-hydroxybnzene
4-Aminobenzenol
EINECS(EC#)
204-616-2
Molecular Formula
C6H7NO
MDL Number
MFCD00007869
Molecular Weight
109.13
MOL File
123-30-8.mol

Chemical Properties

Appearance
o-Aminophenol appears as colorless needles or as white crystalline substance turning tan to brown on exposure to air.
Appearance
Off white granular powder
Melting point 
188 °C
mp 
188 °C
Boiling point 
284 °C
bp 
284 °C
density 
1.29
vapor pressure 
0.4 hPa (110 °C)
refractive index 
1.5444 (estimate)
Fp 
189 °C
storage temp. 
Refrigerator
solubility 
water: slightly soluble
form 
Crystalline Powder
pka
5.48, 10.30(at 25℃)
color 
White to cream
Stability:
Stable, though may discolour in air. Incompatible with acids, chloroformates, strong oxidizing agents.
Water Solubility 
1.5 g/100 mL (20 ºC)
Sensitive 
Air & Light Sensitive
Decomposition 
284 °C
Merck 
14,462
BRN 
385836
Contact allergens
This hair dye is frequently implicated in contact dermatitis in hairdressers, customers, or people sensitized to para-phenylenediamine, by the way of “blackhenna” temporary tattoos.
InChIKey
PLIKAWJENQZMHA-UHFFFAOYSA-N
CAS DataBase Reference
123-30-8(CAS DataBase Reference)
NIST Chemistry Reference
Phenol, 4-amino-(123-30-8)
EPA Substance Registry System
123-30-8(EPA Substance)

Hazard Information

Definition
ChEBI: An amino phenol (one of the three possible isomers) which has the single amino substituent located para to the phenolic -OH group.
General Description
White or reddish-yellow crystals or light brown powder. Turns violet when exposed to light.
Reactivity Profile
Heat (decomposition forming HCN, nitrous vapors, CO); water (CO2); reacts violently with acids, bases, alcohols and amines causing fire and explosion hazards [Handling Chemicals Safely 1980 p. 647].
Air & Water Reactions
Insoluble in water.
Potential Exposure
Workers may be exposed to oAminophenol during its use as a chemical intermediate; in the manufacture of azo and sulfur dyes; and in the photographic industry. There is potential for consumer exposure to o-Aminophenol because of its use in dyeing hair, fur, and leather. The compound is a constituent of 75 registered cosmetic products suggesting the potential for widespread consumer exposure. p-Aminophenol is used mainly as a dye, dye intermediate and as a photographic developer; and in small quantities in analgesic drug preparation. Consumer exposure to p-aminophenol may occur from use as a hairdye or as a component in cosmetic preparations. mAminophenol is used mainly as a dye intermediate
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, including 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 medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
Fire Hazard
Flash point data are not available for this chemical. P-AMINOPHENOL is probably combustible.
Shipping
UN2512 Aminophenols (o-; m-; p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials
Incompatibilities
These phenol/cresol materials can react with oxidizers; reaction may be violent. Incompatible with strong reducing substances such as alkali metals, hydrides, nitrides, and sulfides. Flammable gas (H2) may be generated, and the heat of the reaction may cause the gas to ignite and explode. Heat may be generated by the acidbase reaction with bases; such heating may initiate polymerization of the organic compound. Reacts with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Phenols are sulfonated very readily (e.g., by concentrated sulfuric acid at room temperature). These reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid and can explode when heated. Many phenols form metal salts that may be detonated by mild shock.
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
Synthesis Reference(s)
Synthesis, p. 285, 1971
Tetrahedron Letters, 34, p. 2441, 1993 DOI: 10.1016/S0040-4039(00)60436-7
Health Hazard
p-Aminophenol is of moderately low toxicity but has caused dermal sensitization and kidney injury; the potential for producing methemoglobin is of relatively minor importance.
The oral LD50 in rats was 671 mg/kg.1 Effects included central nervous system depression. A solution of 2.5% applied to abraded skin of rabbits was a mild irritant.1 p- Aminophenol caused dermal sensitization in guinea pigs, and skin sensitization has been reported in humans.2,3 The dermal LD50 in rabbits was greater than 8 g/kg, which strongly suggests that absorption through the skin is minimal.4 Single nonlethal acute doses in rats produced proximal renal tubular necrosis of the pars recta.
Purification Methods
Crystallise it from EtOH, then water, excluding oxygen. It sublimes at 110o/0.3mm. It has been purified by chromatography on alumina with a 1:4 (v/v) mixture of absolute EtOH/*benzene as eluent. [Beilstein 13 IV 1014.]

Safety Data

Hazard Codes 
Xn,N
Risk Statements 
R20/22:Harmful by inhalation and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R68:Possible risk of irreversible effects.
R40:Limited evidence of a carcinogenic effect.
Safety Statements 
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
RIDADR 
UN 2512 6.1/PG 3

WGK Germany 
3

RTECS 
SJ5075000


8
Autoignition Temperature
>250 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
28402090
HS Code 
29222900
Safety Profile
Poison by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. An allergen and skin and eye irritant. Mutation data reported. Can cause contact dermatitis, bronchial asthma, and methemoglobinemia with cyanosis. When heated to decomposition it emits toxic fumes of NOx,.
Hazardous Substances Data
123-30-8(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 375 mg/kg LD50 dermal Rabbit > 10000 mg/kg

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

Questions And Answer

description
4-Aminophenol (or para-aminophenol or p-aminophenol) is the organic compound with the formula H2NC6H4OH, belongs to the class of organic compounds known as aniline and substituted anilines.
Typically available as a white powder, it was commonly used as a developer for black-and-white film, marketed under the name Rodinal.
Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be recrystallized from hot water. In the presence of a base, it oxidizes readily. The methylated derivatives N-methylaminophenol and N,N-dimethylaminophenol are of commercial value.
The compound is one of three isomeric aminophenols, the other two being 2-aminophenol and 3-aminophenol.
Chemical Properties
It is white or light yellow-brown crystals. It is slightly soluble in water and ethanol but insoluble in benzene and chloroform. It will quickly exhibit brown color after being dissolved in alkaline solution.
Uses
It can be used for the production of Sulphur Blue FBG and weak acid dyes such as yellow 5G. It can be used for the manufacturing of drugs such as paracetamol and clofibrate as well as being used as developer and antioxidants, etc.
It can be used as the reagents for the analysis.
The product is the intermediate of pharmaceutical intermediates, dyes and other fine chemicals. It can be used for the production of paracetamol, azo dyes, sulfur dyes, acid dyes, fur dye and developer, antioxidants as well as oil additive.
It is widely used in the synthesis of pharmaceuticals, dyes and other organic products and is mainly for the synthesis of paracetamol, clofibrate ketone, vitamin B1 and compound nicotinamide.
It can be used as the raw material of medicine and dyes, antioxidants and the developer.
It can be used for gold assay as well as determination of copper, iron, magnesium, vanadium, nitrite and cyanate, antioxidants.
Preparation
5 g of phenylhydroxylamine are slowly added to 100 ml of 50% sulphuric acid, cooled in a freezing mixture, 500 ml of water poured in, and the whole boiled until a sample, tested with chromic acid solution, gives a smell of quinone and no smell of nitrobenzene. The liquid is neutralised with sodium bicarbonate, saturated with common salt, and extracted with ether. The ether is removed by evaporation, and the residue washed with cold water and dissolved in hot water. The solution is filtered hot, and cooled, and the 4-aminophenol again extracted with ether. Yield almost theoretical. Colourless crystals; somewhat soluble in water; m.p. 185° C.
Systematic organic chemistry, by W. M. Cumming, 209, 1937.
Acute toxicity
oral-rat LD50: 375 mg/kg; intraperitoneal-mouse LDL0: 100 mg/kg.
Toxicity and protection
It is toxic. The p-amino phenol has double toxicity of both aniline and phenol. Absorption of it through the skin can cause dermatitis as well as cause methemoglobinemia and asthma. The contact of its hydrochloride with the skin can cause severe itching or eczema. Subcutaneous injection-cats-half lethal dose-LD50: 37mg/kg.
Skin irritation data
Rabbit 12.5 mg/24 hours Mild; Eyes-rabbit mild 100 mg.
Flammable and hazardous characteristics
it is combustible upon fire and can be subject to thermal decomposition; burning of it release toxic fumes of nitrogen oxide.

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