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124-09-4

Basic Information
CAS No.: 124-09-4
Name: Hexamethylenediamine
Article Data: 185
Molecular Structure:
Molecular Structure of 124-09-4 (Hexamethylenediamine)
Formula: C6H16N2
Molecular Weight: 116.206
Synonyms: 1,6-Diamino-n-hexane;1,6-Diaminohexane;Advancure;HMDA;Hexamethylenediamine;Hexylenediamine;Hi Perm;NSC 9257;RT Advancure HD;V 1;a,w-Hexanediamine;
EINECS: 204-679-6
Density: 0.89 g/cm3
Melting Point: 42-45 °C
Boiling Point: 205 °C at 760 mmHg
Flash Point: 81.1 °C
Solubility: Slightly soluble in water, but soluble in ethanol, ethyl ether and benzene
Appearance: White to cream solid
Hazard Symbols: CorrosiveC
Risk Codes: 34-37-20/21/22
Safety: 26-36/37/39-45-22-27
Transport Information: UN 2735 8/PG 3
PSA: 52.04000
LogP: 1.86480
Synthetic route
RuHCl(H2)(PCy3)2

RuHCl(H2)(PCy3)2

111-69-3

hexanedinitrile

2797-51-5

quinoclamine

124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
In N-butylamine100%
111-69-3

hexanedinitrile

A

111-49-9

hexamethylene imine

B

124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h; pretreatment is given in full text In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;A 1.1%
B 97%
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;A 1.3%
B 90.1%
With ammonium hydroxide; hydrogen In water; isopropyl alcohol at 130℃; under 41254.1 Torr; for 4h; Autoclave;A 9%
B 90%
With hydrogen; iron catalyst at 140℃; under 233483 Torr;
1080571-11-4

C6H16N2*C7H16N2O2

124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
With 2,5-dimethyl-2-ethyl hexanoic acid In water at 120 - 180℃; for 2h; Product distribution / selectivity;95%
58491-62-6

furan-2,5-dicarbonitrile

124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
With hydrogen; titanium(IV) oxide; platinum In ethanol at 100℃; under 7500.75 Torr; for 4h;95%
111-69-3

hexanedinitrile

124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel; sodium hydroxide In methanol; water at 30 - 60℃;90%
With hydrogen In ethanol at 75℃; under 1500.15 - 15001.5 Torr; for 3h;80%
With ammonia; hydrogen In toluene at 120℃; under 22502.3 Torr; for 16h; Autoclave;75%
13028-54-1

1,6-diazidohexane

124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
With aluminum oxide; potassium hydroxide; hydrazine In neat (no solvent) for 1h; Milling;90%
1072-21-5

hexanedial

124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
With ammonia; hydrogen In methanol at -5 - 0℃; under 41254.1 Torr; for 0.5h; Pressure; Temperature; Autoclave;82%
With Co-doped zirconium dioxide; ammonia; hydrogen; N-butylamine In methanol at 119.84℃; for 10h; Autoclave; chemoselective reaction;63%
629-11-8

1,6-hexanediol

124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
Stage #1: 1,6-hexanediol With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia In toluene at 0℃; under 3750.38 Torr; for 1h; Autoclave;
Stage #2: In toluene at 155℃; for 16h; Autoclave;
81%
With ammonium hydroxide; 4.04 wt.% ruthenium and 0.7 wt.% rhenium on carbon; ammonia at 160℃; under 5175.52 - 35253.5 Torr; for 3h; Reagent/catalyst; Inert atmosphere;23.4%
With ammonia at 220 - 260℃;
111-69-3

hexanedinitrile

A

124-09-4

1,6-Hexanediamine

B

2432-74-8

1-amino-5-cyanopentane

Conditions
ConditionsYield
With Rh/Al2O3; hydrogen In ethanol at 80℃; for 6h;A 24.4%
B 75.6%
With hydrogen; active elemental iron component In ammonia at 70 - 220℃; under 75007.5 - 300030 Torr;
Stage #1: hexanedinitrile With potassium hydroxide; hydrogen; nickel at 50℃; under 15001.5 Torr;
Stage #2: With phosphoric acid Purification / work up;

C-(6-Methoxy-2-p-tolyl-quinolin-4-yl)-N-[6-(6-methoxy-2-p-tolyl-quinolin-4-ylmethanesulfonylamino)-hexyl]-methanesulfonamide

A

124-09-4

1,6-Hexanediamine

B

117839-37-9

6-methoxy-2-(p-tolyl)quinoline

C

117839-39-1

6-methoxy-4-methyl-2-(p-tolyl)quinoline

Conditions
ConditionsYield
In isopropyl alcohol Irradiation; 350 nm;A 32%
B n/a
C n/a
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Specification

This product is an organic compound with the formula C6H16N2. The systematic name of this chemical is 1,6-Hexanediamine. It belongs to the product categories of Industrial/Fine Chemicals; alpha,omega-Alkanediamines; alpha,omega-Bifunctional Alkanes; Monofunctional & alpha,omega-Bifunctional Alkanes. Its EINECS number is 204-679-6. With the CAS registry number 124-09-4, it is also named as Hexamethylenediamine. In addition, the molecular weight is 116.20. Its classification code is Reproductive Effect. It is stable in air but combustible. Like all organic compounds, it is incompatible with strong oxidants. It should be sealed and stored in a ventilated and dry place. Moreover, it should be protected from heat, moisture and fire. Hexamethylenediamine is used almost exclusively for the production of polymers, an application that takes advantage of its bifunctional structure. The great majority of the diamine is consumed by the production of nylon 6-6 via condensation with adipic acid. Otherwise hexamethylene diisocyanate (HDI) is generated from this diamine as a monomer feedstock in the production of polyurethane. The diamine also serves as a cross-linking agent in epoxy resins.

Physical properties of 1,6-Hexanediamine are: (1)ACD/LogP: 0.04; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 2; (8)#H bond donors: 4; (9)#Freely Rotating Bonds: 7; (10)Polar Surface Area: 52.04 Å2; (11)Index of Refraction: 1.459; (12)Molar Refractivity: 36.91 cm3; (13)Molar Volume: 134.9 cm3; (14)Polarizability: 14.63×10-24cm3; (15)Surface Tension: 35.3 dyne/cm; (16)Density: 0.861 g/cm3; (17)Flash Point: 81.1 °C; (18)Enthalpy of Vaporization: 44.13 kJ/mol; (19)Boiling Point: 205 °C at 760 mmHg; (20)Vapour Pressure: 0.256 mmHg at 25°C.

Preparation of 1,6-Hexanediamine: this chemical can be prepared by hexanedinitrile with hydrogen generated in situ electrochemically on Raney nickel electrod. This reaction will need reagents H2, NaOMe and solvent methanol. This reaction will also need catalyst Raney nickel. The yield is about 70%.

1,6-Hexanediamine can be prepared by hexanedinitrile with hydrogen generated in situ electrochemically on Raney nickel electrod

Uses of 1,6-Hexanediamine: it can be used to produce N-(6-aminohexyl)trifluoroacetamide at the temperature of -78 - 0 °C. It will need solvent methanol with the reaction time of 2.5 hours. The yield is about 95%.

1,6-Hexanediamine can be used to produce N-(6-aminohexyl)trifluoroacetamide at the temperature of -78 - 0 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to respiratory system and can cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should not breathe dust and must take off immediately all contaminated clothing. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you need seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: NCCCCCCN
(2)Std. InChI: InChI=1S/C6H16N2/c7-5-3-1-2-4-6-8/h1-8H2
(3)Std. InChIKey: NAQMVNRVTILPCV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LCLo inhalation 750mg/m3/10M (750mg/m3)   National Defense Research Committee, Office of Scientific Research and Development, Progress Report.Vol. NDCrc-132, Pg. SEP1942。
mouse LD50 intraperitoneal 320mg/kg (320mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 43(11), Pg. 110, 1978.
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02313。
mouse LD50 subcutaneous 1300mg/kg (1300mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 74, 1982.
rabbit LD50 skin 1110mg/kg (1110mg/kg)   Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977.
rat LC inhalation > 950mg/m3/4H (950mg/m3)   United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. Vol. 8EHQ-1090-0979.
rat LD50 oral 750mg/kg (750mg/kg)   Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977.