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1,8-Diaminooctane, also known as alkane-alpha,omega-diamine, is an organic compound characterized by the presence of two amino groups separated by eight methylene groups. It is derived from a hydride of an octane and is typically found as a white to yellowish solidified crystalline mass. This versatile compound is widely used in various industries due to its unique chemical properties and reactivity.

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  • 373-44-4 Structure
  • Basic information

    1. Product Name: 1,8-Diaminooctane
    2. Synonyms: 1,8-OCTANEDIAMINE;1,8-DIAMINOOCTANE;RARECHEM AL BW 0084;OCTAMETHYLENDIAMINE;OCTAMETHYLENEDIAMINE;1,4-Octanediamine;1,8-Octamethylenediamine;1,8-Octylenediamine
    3. CAS NO:373-44-4
    4. Molecular Formula: C8H20N2
    5. Molecular Weight: 144.26
    6. EINECS: 206-764-3
    7. Product Categories: alpha,omega-Alkanediamines;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Polyamines
    8. Mol File: 373-44-4.mol
  • Chemical Properties

    1. Melting Point: 50-52 °C(lit.)
    2. Boiling Point: 225-226 °C(lit.)
    3. Flash Point: 329 °F
    4. Appearance: White to yellow/Solidified Crystalline Mass
    5. Density: 0.98 g/mL at 20 °C
    6. Vapor Pressure: 0.0378mmHg at 25°C
    7. Refractive Index: 1.4618 (estimate)
    8. Storage Temp.: 2-8°C
    9. Solubility: 575g/l
    10. PKA: 11.00, 10.1(at 20℃)
    11. Explosive Limit: 1.1-6.8%(V)
    12. Water Solubility: 575 g/L (20 ºC)
    13. Sensitive: Hygroscopic
    14. BRN: 1735426
    15. CAS DataBase Reference: 1,8-Diaminooctane(CAS DataBase Reference)
    16. NIST Chemistry Reference: 1,8-Diaminooctane(373-44-4)
    17. EPA Substance Registry System: 1,8-Diaminooctane(373-44-4)
  • Safety Data

    1. Hazard Codes: C,Xi
    2. Statements: 34-36/37/38
    3. Safety Statements: 26-36/37/39-45-37/39
    4. RIDADR: UN 3259 8/PG 3
    5. WGK Germany: 3
    6. RTECS: RG8841500
    7. F: 3-9-23
    8. HazardClass: 8
    9. PackingGroup: III
    10. Hazardous Substances Data: 373-44-4(Hazardous Substances Data)

373-44-4 Usage

Uses

1,8-Diaminooctane is used as a crucial raw material and intermediate in the field of organic synthesis, contributing to the development of new compounds and materials. Its ability to form covalent bonds with a wide range of molecules makes it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 1,8-Diaminooctane is utilized as a building block for the synthesis of various drugs and drug candidates. Its unique structure allows for the creation of complex molecular architectures, which can be tailored to target specific biological pathways or receptors, leading to the development of novel therapeutic agents.
Used in Agrochemical Industry:
1,8-Diaminooctane is also employed in the agrochemical industry as a key intermediate for the synthesis of pesticides, herbicides, and other crop protection agents. Its reactivity and structural diversity enable the development of effective and targeted agrochemicals that can protect crops from pests and diseases while minimizing environmental impact.
Used in Dye Industry:
In the dye industry, 1,8-Diaminooctane serves as an essential intermediate for the production of various types of dyes. Its ability to form stable complexes with other molecules allows for the creation of dyes with specific color properties and improved stability, making it a valuable component in the development of new dye formulations.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. Asevere skin and eye irritant. When heated todecomposition it emits toxic vapors of NOx.

Purification Methods

Distil the diamine under vacuum in an inert atmosphere (N2 or Ar), cool and store the distillate in an inert atmosphere in the dark. The dihydrochloride has m 273-274o. [Nae & Le Helv Chim Acta 15 55 1955, Beilstein 4 III 612.]

Check Digit Verification of cas no

The CAS Registry Mumber 373-44-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,7 and 3 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 373-44:
(5*3)+(4*7)+(3*3)+(2*4)+(1*4)=64
64 % 10 = 4
So 373-44-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H20N2/c9-7-5-3-1-2-4-6-8-10/h1-10H2/p+2

373-44-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (B23885)  1,8-Diaminooctane, 98%   

  • 373-44-4

  • 25g

  • 360.0CNY

  • Detail
  • Alfa Aesar

  • (B23885)  1,8-Diaminooctane, 98%   

  • 373-44-4

  • 100g

  • 953.0CNY

  • Detail
  • Aldrich

  • (D22401)  1,8-Diaminooctane  98%

  • 373-44-4

  • D22401-25G

  • 438.75CNY

  • Detail
  • Aldrich

  • (D22401)  1,8-Diaminooctane  98%

  • 373-44-4

  • D22401-100G

  • 1,096.29CNY

  • Detail

373-44-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,8-diaminooctane

1.2 Other means of identification

Product number -
Other names Octamethylenediamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:373-44-4 SDS

373-44-4Relevant articles and documents

Multi-enzymatic cascade reactions with Escherichia coli-based modules for synthesizing various bioplastic monomers from fatty acid methyl esters?

Jung, Hyunsang,Kim, Byung-Gee,Kim, Ye Chan,Park, Beom Gi,Patil, Mahesh D.,Sarak, Sharad,Yoo, Hee-Wang,Yun, Hyungdon

supporting information, p. 2222 - 2231 (2022/04/03)

Multi-enzymatic cascade reaction systems were designed to generate biopolymer monomers using Escherichia coli-based cell modules, capable of carrying out one-pot reactions. Three cell-based modules, including a ω-hydroxylation module (Cell-Hm) to convert fatty acid methyl esters (FAMEs) to ω-hydroxy fatty acids (ω-HFAs), an amination module (Cell-Am) to convert terminal alcohol groups of the substrate to amine groups, and a reduction module (Cell-Rm) to convert the carboxyl groups of fatty acids to alcohol groups, were constructed. The product-oriented assembly of these cell modules involving multi-enzymatic cascade reactions generated ω-ADAs (up to 46 mM), α,ω-diols (up to 29 mM), ω-amino alcohols (up to 29 mM) and α,ω-diamines (up to 21 mM) from 100 mM corresponding FAME substrates with varying carbon chain length (C8, C10, and C12). Finally 12-ADA and 1,12-diol were purified with isolated yields of 66.5% and 52.5%, respectively. The multi-enzymatic cascade reactions reported herein present an elegant ‘greener’ alternative for the biosynthesis of various biopolymer monomers from renewable saturated fatty acids.

METHOD FOR PREPARING DICYANOALKANE AND BIS(AMINOMETHYL)ALKANE

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Paragraph 0097; 0098, (2021/05/14)

A method for preparing a dicyanoalkane may omit a filtration for a catalyst after a cyanation reaction can by carrying out the cyanation reaction in a state in which precipitation of a metal catalyst is suppressed. A method for preparing a dicyanoalkane may involve cyanating one or more aliphatic dicarboxylic acids and/or salt(s) thereof with an ammonia source in the presence of a predetermined compound and a catalyst, wherein, in the cyanation, the amount of the predetermined compound is maintained at a predetermined amount or more with respect to the catalyst.

Method for producing aliphatic diamine (by machine translation)

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Paragraph 0054; 0055, (2019/07/05)

[Problem] safety, yield, at least one aliphatic diamine having improved simplicity in terms of the method. (1) Formula (2) represented by the formula [a] or the aliphatic diamide, sodium hypochlorite, the presence of a base, a water and alcohol mixture containing alcohol in a solvent comprises the step of - the reaction, the molar ratio of the aliphatic diamide basic, aliphatic diamide (molar ratio)=1.8 - 6.0 in/base, production of aliphatic diamine. [Drawing] no (by machine translation)

Imprinted Apportionment of Functional Groups in Multivariate Metal-Organic Frameworks

Feng, Liang,Wang, Kun-Yu,Lv, Xiu-Liang,Powell, Joshua A.,Yan, Tian-Hao,Willman, Jeremy,Zhou, Hong-Cai

supporting information, p. 14524 - 14529 (2019/10/02)

Sophisticated chemical processes widely observed in biological cells require precise apportionment regulation of building units, which inspires researchers to develop tailorable architectures with controllable heterogeneity for replication, recognition and information storage. However, it remains a substantial challenge to endow multivariate materials with internal sequences and controllable apportionments. Herein, we introduce a novel strategy to manipulate the apportionment of functional groups in multivariate metal-organic frameworks (MTV-MOFs) by preincorporating interlocked linkers into framework materials. As a proof of concept, the imprinted apportionment of functional groups within ZIF-8 was achieved by exchanging imine-based linker templates with original linkers initially. The removal of linker fragments by hydrolysis can be achieved via postsynthetic labilization, leading to the formation of architectures with controlled heterogeneity. The distributions of functional groups in the resulting imprinted MOFs can be tuned by judicious control of the interlocked chain length, which was further analyzed by computational methods. This work provides synthetic tools for precise control of pore environment and functionality sequences inside multicomponent materials.

Parallel anti-sense two-step cascade for alcohol amination leading to ω-amino fatty acids and α,ω-diamines

Sung, Sihyong,Jeon, Hyunwoo,Sarak, Sharad,Ahsan, Md Murshidul,Patil, Mahesh D.,Kroutil, Wolfgang,Kim, Byung-Gee,Yun, Hyungdon

supporting information, p. 4591 - 4595 (2018/10/23)

Running two two-step cascades in parallel anti-sense to transform an alcohol to an amine allowed the conversion of ω-hydroxy fatty acids (ω-HFAs) and α,ω-diols to the corresponding ω-amino fatty acids (ω-AmFAs) and α,ω-diamines, respectively. The network required only two enzymes namely an aldehyde reductase (AHR) and a transaminase (TA). Benzylamine served on the one hand as amine donor and on the other hand after deamination to benzaldehyde also as oxidant. All ω-HFAs tested were efficiently transformed to their corresponding ω-AmFAs using purified enzymes as well as a whole-cell system, separately expressing both the enzymes, with conversions ranging from 80-95%. Additionally, a single-cell co-expressing all enzymes successfully produced the ω-AmFAs as well as the α,ω-diamines with >90% yield. This system was extended by employing a lactonase, enabling the transformation of ?-caprolactone to its corresponding ω-AmFA with >80% conversion.

Highly efficient nitrobenzene and alkyl/aryl azide reduction in stainless steel jars without catalyst addition

Martina, Katia,Baricco, Francesca,Tagliapietra, Silvia,Moran, Maria Jesus,Cravotto, Giancarlo,Cintas, Pedro

supporting information, p. 18881 - 18888 (2018/11/26)

The mechanochemical and selective reduction of aryl nitro and aryl/alkyl azide derivatives, with either formate salts or hydrazine, to the corresponding, synthetically useful amines occurs in excellent yields in a planetary ball mill without the addition of a catalyst. This newly developed and solvent-free protocol is efficient, fast and does not require the addition of a metal hydrogenation catalyst as the stainless steel jar itself fulfils that role. The method has been applied to a broad range of compounds and excellent yields have been obtained. The formylation of alkyl amines has been successfully performed, by means of mechanochemical activation, in the presence of ammonium formate alone.

Diamine compound (by machine translation)

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Paragraph 0082; 0083; 0086; 0087, (2017/07/26)

[Problem] to obtain, dicyano compound is reacted with hydrogen, resulting diamine compound impurities contained in elucidating structure, the impurity content is reduced, a high purity in a high yield in an industrially suitable method for producing a diamine compound. [Solution] nickel catalyst in the presence of a basic compound, a compound represented by general formula (1) is reacted with hydrogen shown dicyano, method for producing a diamine compound, a diamine compound represented by general formula (3) contained in the obtained amide compound content of 0.5% or less as measured by gas chromatography indicated by the area of the, the diamine compound. (1) NC-a Z-to-CN(Z may, of 1 - 20 carbon atoms of straight-chain alkylene group, an alkylene group of a carbon number of 3 - 20 annular, or branched alkylene group of a carbon number of 3 - 20. )(Z is, the synonymous. )[Drawing] no (by machine translation)

Cavitands as Reaction Vessels and Blocking Groups for Selective Reactions in Water

Masseroni, Daniele,Mosca, Simone,Mower, Matthew P.,Blackmond, Donna G.,Rebek, Julius

, p. 8290 - 8293 (2016/07/19)

The majority of reactions currently performed in the chemical industry take place in organic solvents, compounds that are generally derived from petrochemicals. To promote chemical processes in water, we examined the use of synthetic, deep water-soluble cavitands in the Staudinger reduction of long-chain aliphatic diazides (C8, C10, and C12). The diazide substrates are taken up by the cavitand in D2O in folded, dynamic conformations. The reduction of one azide group to an amine gives a complex in which the substrate is fixed in an unsymmetrical conformation, with the amine terminal exposed and the azide terminal deep and inaccessible within the cavitand. Accordingly, the reduction of the second azide group is inhibited, even with excess phosphine, and good yields of the monofunctionalized products are obtained. In contrast, the reduction of the free diazides in bulk solution yields diamine products.

DIAMINE COMPOUNDS, DINITRO COMPOUNDS AND OTHER COMPOUNDS, AND METHODS OF PRODUCING THEREOF AND USES RELATED THEREOF

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Paragraph 0625, (2016/03/22)

Provided herein are (phenylene)dialkanamines, and methods of producing such (phenylene)dialkanamines from various furanyl and benzyl compounds. Such furanyl compounds may include, for example, bis(nitroalkyl)furans, bis(aminoalkyl)furans, and nitroalkyl(furan)acetonitriles. Such compounds may include, for example, bis(nitroalkyl)benzenes. Provided herein are also alkyldiamines, and methods for producing such alkyldiamines from furanyl compounds.

ACYCLIC ALKENES VIA OZONOLYSIS OF MULTI-UNSATURATED CYCLOALKENES

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Paragraph 00158, (2015/02/02)

A method of making a compound of formula (IIa) by selective ozonolysis of a compound of formula (I) is provided, wherein A is a C6-C10 alkene chain with at least one double bond, R1 is a C1-C10 alkyl, and R3 is an oxygen-containing functional group.

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