80-52-4

Basic information

• Product Name: 1,8-DIAMINO-P-MENTHANE
• Synonyms: 4-(1-Amino-1-methylethyl)-1-methylcyclohexanamine;4-amino-.alpha.,.alpha.-4-trimethyl-Cyclohexanemethanamine;4-Amino-alpha,alpha,4-trimethylcyclohexanemethamine;4-amino-alpha,alpha,4-trimethyl-cyclohexanemethanamin;ai3-23799;Menthanediamine;nsc5612;p-Menthane-1,8-diamine
• CAS NO: 80-52-4
• Molecular Formula: C₁₀H₂₂N₂
• Molecular Weight: 170.3
• EINECS: 201-287-7
• Product Categories: Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 80-52-4.mol

Chemical Properties

• Melting Point: −45 °C(lit.)
• Boiling Point: 107-126 °C10 mm Hg(lit.)
• Flash Point: 200 °F
• Appearance: /
• Density: 0.914 g/mL at 25 °C(lit.)
• Vapor Pressure: 10 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.4805(lit.)
• Storage Temp.: 2-8°C
• PKA: 11.02±0.70(Predicted)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 1,8-DIAMINO-P-MENTHANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-DIAMINO-P-MENTHANE(80-52-4)
• EPA Substance Registry System: 1,8-DIAMINO-P-MENTHANE(80-52-4)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• RTECS: OS8925000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 80-52-4(Hazardous Substances Data)

Usage

Uses

Used in Epoxy Resin Industry:
1,8-Diamino-p-menthane is used as a curing agent for epoxy resins, enhancing their cross-linking and improving the final product's mechanical and thermal properties.
Used in Chemical Synthesis:
1,8-Diamino-p-menthane serves as a chemical intermediate, facilitating the synthesis of various compounds and contributing to the development of new materials and products.
Used in Coordination Chemistry:
1,8-Diamino-p-menthane is used in the synthesis of Schiff bases, which are then utilized in the preparation of coordination complexes with Cu(II), Zn(II), Cr(III), Fe(III), and Co(III) ions. These complexes have potential applications in various fields, such as catalysis, materials science, and bioinorganic chemistry.
Used in Agrochemical Industry:
As a precursor, 1,8-diamino-p-menthane is used to synthesize heterocyclic Schiff base derivatives that exhibit herbicidal activity, contributing to the development of effective and environmentally friendly weed control agents.

Air & Water Reactions

Slightly water soluble .

Reactivity Profile

1,8-DIAMINO-P-MENTHANE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Hazard

Strong irritant to eyes and skin, calls for eye protection.

Fire Hazard

1,8-DIAMINO-P-MENTHANE is combustible.

InChI:InChI=1/C10H20.2H3N/c1-8(2)10-6-4-9(3)5-7-10;;/h8-10H,4-7H2,1-3H3;2*1H3

Upstream product

• 74-90-8 hydrogen cyanide 
• 98-55-5 terpineol 
• 99977-24-9 1,8-dinitro-p-menthane 
• 64374-25-0 1,8-Diazido-p-menthan 
• 64-19-7 acetic acid 
• 64374-19-2 8-Azido-1-hydroxy-trans-p-menthan 
• 64374-26-1 N-(2-(4-acetamido-4-methylcyclohexyl)propan-2-yl)acetamide 
• 80-56-8 Pinene 
• 112766-74-2 1,8-p-menthane dibenzamide 
• 138-86-3 limonene. 
• 99-85-4 crithmene 
• 80-53-5 terpin hydrate 
• 565-48-0 cis-1,8-terpine 

Downstream Products

• 14002-20-1 N,N'-dimethylene-p-menthane-1,8-diyldiamine 
• 99977-24-9 1,8-dinitro-p-menthane 
• 5116-72-3 p-menthane-1,8-diyl diisocyanate 
• 112766-74-2 1,8-p-menthane dibenzamide 
• 13908-64-0 1-(2-Chloro-ethyl)-3-(4-{1-[3-(2-chloro-ethyl)-ureido]-1-methyl-ethyl}-1-methyl-cyclohexyl)-urea 
• 96535-25-0 1-Guanidino-1-methyl-4-<α-guanidino-isopropyl>-cyclohexan 
• 35046-17-4 1,8-Dipropionamido-p-menthan 
• 64374-26-1 N-(2-(4-acetamido-4-methylcyclohexyl)propan-2-yl)acetamide 
• 1295584-37-0 1,8-bis(2-thiophenecarboxamido)-p-menthane 
• 1295584-38-1 1,8-bis(2-furancarboxamido)-p-menthane 

Relevant articles and documents

Method for preparingp-menthane-1,8-diamine by one-step method

The invention provides a method for preparing p-menthane-1,8-diamine by a one-step method, which comprises the following steps: by taking unsaturated turpentine monoterpene as a reaction raw material, strong protonic acid as a reaction raw material and a nitrogen-containing inorganic compound as a reaction raw material, carrying out one-step reaction in water, and after the reaction is completed, conducting extracting and carrying out reduced pressure distillation to obtain a p-menthane-1,8-diamine purified product. The method provided by the invention has the advantages of few steps, easy purification, direct preparation of p-menthane-1,8-diamine by a one-step method, high product purity and high yield, byproducts are carbon dioxide and sulfate, and the sulfate can be directly treated after gas is subjected to absorption treatment. According to the invention, the unsaturated turpentine monoterpene, the strong protonic acid and the nitrogen-containing inorganic compound are jointly used as reaction raw materials for the first time, so that the one-step reaction can be realized, and the technical defect that the one-step reaction cannot be realized by a synthesis thought that protonic acid is used as a catalyst in a traditional preparation method is overcome.

Method for preparing 1 and 8 - P-menthane diamine from 1 and 8 - P-menthane diethanolamide

The invention discloses a method for preparing 1,8-paramylenediamine from 1,8-paramenthane diethylamide. The method comprises the steps: dissolving raw material 1,8-paramenthane diethylamide togetherwith an inorganic strong alkali in an organic solvent, in a sealed reaction kettle with the pressure of 0 MPa-2.0 MPa, carrying out a reaction for 10 h-20 h at the temperature of 150 DEG C-200 DEG C,filtering the reaction liquid, washing with water and distilling to obtain the product 1,8-paramylenediamine. According to the process, the conversion rate of the raw material 1,8-paramenthane diethylamide is greater than 95%, the maximum conversion rate is up to 100%, the selectivity of the product 1,8-paramylenediamine product is more than 90%, the maximum selectivity is up to 97%, the solvent is cheap and reusable, unreacted alkali and generated acetate can be recovered, the product is easily separated and has high yield, and the method has the advantages of simple operation, environmentalfriendliness, high economy and the like.

Method for preparing 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine from unsaturated turpentine monoterpene

The invention discloses a method for preparing 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine from unsaturated turpentine monoterpene. The unsaturated turpentine monoterpene is used as a raw material and takes a reaction with organic nitrile under the catalysis of strong protonic acid; after full reaction, reaction liquid is neutralized into a neutral state; a non-water-soluble organic solvent is added for extraction; an organic layer is collected and is subjected to still standing; 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine crystals are separated out. 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine solid is hydrolyzed in a polyatomic alcohol solution of inorganic strong base to obtain 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine crude products; negative pressure distillation is performed to obtain 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine pure products. The yield of the 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine product obtained by the method is high; the purity is high. Compared with the existing preparation method, the method has the advantages that the unsaturated turpentine monoterpene which has low cost and is easy to obtain is used as the raw material; the process route is simple; the production cost of the 4-amino-alpha, alpha,4-trimethyl-cyclohexanemethanamine can be effectively reduced; in addition, the method also has the advantages of low toxicity, simple operation process and the like.

Synthesis and Herbicidal Activities of p-Menth-3-en-1-amine and Its Schiff Base Derivatives

p-Menth-3-en-1-amine, 4, and its Schiff base derivatives, 5a-l, were designed and synthesized. They were characterized by FT-IR, ESI+-MS, HRMS, 1H NMR, and 13C NMR spectral analyses, and their pre-emergence herbicidal activities against ryegrass were evaluated. All of the compounds showed excellent herbicidal activity. The Schiff bases showed stronger herbicidal activities than the original amine 4. These compounds showed herbicidal activities comparable to that of glyphosate. The herbicidal activities of 5k and 5l against ryegrass shoot growth were 78.3 and 355.6% higher than that of glyphosate, respectively. Furthermore, the introduction of a chlorine or bromine atom into the Schiff base derivatives containing a furan or benzene ring was beneficial to increase the activity. However, the herbicidal activities were not clearly affected when the heteroatom of the five-membered heterocyclic Schiff base or the position of the substituent on pyridine Schiff base was altered.

Process for preparing 1-oxa-3,8-diaza-4-oxo-spiro-[4,5]-decanes

1-Oxa-3,8-diaza-4-oxo-spiro-[4,5]-decane compounds of the formula STR1 are new light stabilizers for protecting polymers from the damaging effect of UV radiation.