CAS No.92-87-5,Benzidine Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	92-87-5
Name:	Benzidine
Article Data:	256

Formula:	C₁₂H₁₂N₂
Molecular Weight:	184.241
Synonyms:	Benzidine(8CI);4,4'-Bianiline;4,4'-Biphenyldiamine;4,4'-Diamino-1,1'-biphenyl;4,4'-Diaminobiphenyl;4,4'-Diaminodiphenyl;4,4'-Diphenylenediamine;4-(4-Aminophenyl)aniline;4'-Amino-[1,1'-biphenyl]-4-ylamine;C.I. Azoic DiazoComponent 112;Fast Corinth Base B;NSC 146476;p,p'-Bianiline;p,p'-Diaminobiphenyl;p-Diaminodiphenyl;
EINECS:	202-199-1
Density:	1.156 g/cm³
Melting Point:	127-128 °C
Boiling Point:	358.7 °C at 760 mmHg
Flash Point:	203.5 °C
Solubility:	Sparingly soluble in water. <0.1 g/100 mL at 22 °C
Appearance:	off-white solid
Hazard Symbols:	T,N,F,Xn
Risk Codes:	45-22-50/53-52/53-39/23/24/25-23/24/25-11-36/37/38-20/21/22
Safety:	53-45-60-61-36/37-16-7-36-26
Transport Information:	UN 1885 6.1/PG 2
PSA:	52.04000
LogP:	3.68040

Synthetic route

: 92-86-4
4-(4-bromophenyl)bromobenzene

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water; ethylene glycol at 110 - 140℃; for 16h;	100%
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	79%

: 540-37-4
p-aminoiodobenzene

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With magnesium In water at 100℃; for 2h; Sealed tube;	96%
With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide Buchwald-Hartwig Coupling;	75%
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 8h; Electrochemical reaction;	38%

: 1528-74-1
4,4'-dinitrobiphenyl

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With hydrazine In methanol at 50℃;	95%
With sodium tetrahydroborate In ethanol at 24.84℃; for 2h;	95%
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;	93%

: 106-47-8
4-chloro-aniline

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With carbon dioxide; aluminium; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 65℃; under 116262 Torr; for 16h; Ullmann reaction;	95%
With 4-(3'-butyl-1'-imidazolio)-1-butanesulfonic acid hydrogen sulfate; aluminium In carbon dioxide at 45℃; under 116262 Torr; for 16h; Ullmann reaction; Supercritical conditions;	94%
With sulphonic acid functionalized porphyrin meso-substituted triazolium anchored ionic liquid at 20℃; for 16h; Catalytic behavior; Time; Ullmann Condensation; Irradiation;	91%

: 106-40-1
4-bromo-aniline

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With palladium 10% on activated carbon; potassium acetate; bis(pinacol)diborane In ethanol at 60℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	94.3%
With potassium carbonate In N,N-dimethyl-formamide for 0.75h;	90%
With magnesium In water at 100℃; for 3.5h; Sealed tube;	85%

: 3001-15-8
4,4'-diiodobiphenyl

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 25℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;	91%

: 1221066-38-1
N4,N4'-bis(diphenylmethylene)biphenyl-4,4'-diamine

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 2h;	82%

: 586-78-7
para-nitrophenyl bromide

A: 106-40-1
4-bromo-aniline

B: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;	A 82% B 7%

: 89415-43-0
(4-aminophenyl)boronic acid

: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; potassium carbonate In water; acetone for 3h;	80%

: 122-66-7
diphenyl hydrazine

A: 492-17-1
2,4'-diaminobiphenyl

B: 92-87-5
p,p'-diaminobiphenyl

Conditions

Conditions	Yield
In ethanol; water	A 30% B 70%
With hydrogenchloride; lithium chloride In ethanol at 0℃; for 0.5h; Product distribution; kinetic isotope effects; reaction of var. labeled hydrazobenzenes, var. time;	A 91.5 mg B 15.8%
With hydrogenchloride; lithium chloride In ethanol at 0℃; for 0.5h;	A 91.5 mg B 15.8%

Raw Materials

1528-74-1

56-81-5

7440-66-6

60-29-7

540-37-4

7783-06-4

2515-46-0

122-66-7

Downstream Products

135-68-2

531-85-1

92-86-4

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Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Human Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 1 , (World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)(1972),p. 80. ; Human Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 , (World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)(1982),p. 149. ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 1 , (World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)(1972),p. 80. ; IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 , (World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210)(1982),p. 149. . EPA Genetic Toxicology Program. Community Right-To-Know List. Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: OSHA: Cancer Suspect Agent
ACGIH TLV: Confirmed Human Carcinogen
DFG MAK: Human Carcinogen
DOT Classification: 6.1; Label: Poison

Analytical Methods

For occupational chemical analysis use OSHA: #ID-65 or NIOSH: Benzidine in Urine (TLC), 8304; Benzidine in Urine (GC), 8306.

Specification

The Benzidine with CAS registry number of 92-87-5 is also known as [1,1'-Biphenyl]-4,4'-diamine. The IUPAC name is 4-(4-Aminophenyl)aniline. It belongs to product categories of Intermediates of Dyes and Pigments; Azo dye; Amines; Aromatics; Method 8270More...Close...;8000 Series Solidwaste Methods; Analytical Standards; AromaticsChemical Class; AromaticsMethod Specific; BenzidinesEPA; Chemical Class; A-BMethod Specific; Aryl Amines MAK III, Category 1Alphabetic; Alpha Sort; B; BA - BHEnvironmental Standards; Benzidines; Oeko-Tex Standard 100; Volatiles/ Semivolatiles. Its EINECS registry number is 202-199-1. In addition, the formula is C₁₂H₁₂N₂ and the molecular weight is 184.24.

Physical properties about Benzidine are: (1)ACD/LogP: 1.56; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.5; (4)ACD/LogD (pH 7.4): 1.56; (5)ACD/BCF (pH 5.5): 7.83; (6)ACD/BCF (pH 7.4): 9.06; (7)ACD/KOC (pH 5.5): 145.68; (8)ACD/KOC (pH 7.4): 168.41; (9)#H bond acceptors: 2; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 6.48Å²; (13)Index of Refraction: 1.667; (14)Molar Refractivity: 59.31 cm³; (15)Molar Volume: 159.2 cm³; (16)Polarizability: 23.51×10^-24cm³; (17)Surface Tension: 54.2 dyne/cm; (18)Density: 1.156 g/cm³; (19)Flash Point: 203.5 °C; (20)Enthalpy of Vaporization: 60.43 kJ/mol; (21)Boiling Point: 358.7 °C at 760 mmHg; (22)Vapour Pressure: 2.5E-05 mmHg at 25 °C.

Preparation of Benzidine: it is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry.

Benzidine is prepared in a two step process from nitrobenzene.

Uses of Benzidine: it has been significantly withdrawn from use in most industries because it is so carcinogenic. In the past, benzidine was used to test for blood. An enzyme in blood causes the oxidation of benzidine to a distinctively blue-coloured derivative. The test for cyanide relies on similar reactivity. Such applications have largely been replaced by methods using phenolphthalein/hydrogen peroxide and luminol.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. This chemical is very toxic to aquatic organisms and may cause long-term adverse effects in the aquatic environment. Besides, it's danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. This chemical even may cause cancer. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition and keep container tightly closed. This material and its container must be disposed of as hazardous waste. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. What's more, if you feel unwell seek or accident happens medical advice immediately.

You can still convert the following datas into molecular structure:
1. SMILES: c2c(c1ccc(N)cc1)ccc(N)c2
2. InChI: InChI=1/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
3. InChIKey: HFACYLZERDEVSX-UHFFFAOYAX
4. Std. InChI: InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2
5. Std. InChIKey: HFACYLZERDEVSX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
dog	LDLo	oral	200mg/kg (200mg/kg)	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 58, Pg. 167, 1907.
mouse	LD50	intraperitoneal	110mg/kg (110mg/kg)	Progress in Mutation Research. Vol. 1, Pg. 682, 1981.
mouse	LD50	oral	214mg/kg (214mg/kg)	National Technical Information Service. Vol. PB214-270,
rabbit	LDLo	oral	200mg/kg (200mg/kg)	Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 58, Pg. 167, 1907.
rat	LD50	oral	309mg/kg (309mg/kg)	National Technical Information Service. Vol. PB214-270,